Facile one-pot transformation of carboxylic acid chlorides into 2-substituted allyl alcohols or epichlorohydrins

Treatment of carboxylic acid chlorides (1) with chloromethyl-lithium generated in situ(1 : 2 molar ratio) in the presence of lithium iodide leads, after hydrolysis, to the corresponding homologated 2-substituted allyl alcohols (2). When the same reaction is carried out using iodide-free butyl-lithium, instead of methyl-lithium-lithium iodide, the corresponding 2-substituted epichlorohydrins (5) are formed.